This Week in Startups E2206: IPO Mania hits the TWiST 500! Three companies are ready to go public

Host: Jason Calacanis
Co-host: Alex Wilhelm
Date: November 10, 2025

Episode Overview

In this episode, Jason reports live from Tokyo and joins Alex for an exploration of the tech startup landscape, zooming in on the approaching IPO wave featuring standout companies from the TWiST 500. The hosts dive deep into:

• Early signals of an AI-driven employment shift
• The recent controversy involving Marc Andreessen and the Pope
• Macro worries and “bubble” behaviors in Silicon Valley
• Razor-sharp breakdowns of soon-to-IPO success stories: Ledger, 1Password, Mercury, and Gamma
• Hot-button labor and management disputes in tech

The conversation is fast-paced, sharp-witted, and loaded with candid observations about founder mindsets, investment bubbles, and the changing playbook for startup success.

Key Discussion Points & Insights

1. Global Startup Trends: Jason’s World Tour & Founder University

• [02:10] Jason shares excitement about hosting Founder University in Tokyo after its recent success in Riyadh, emphasizing hands-on, tailored support for smaller cohorts of founders.
  • "If you're going to meet with each company every week, you got to keep it to probably 50 or less... you want it to be bespoke." – Jason Calacanis [02:53]
• Discussion of Japan as a vibrant, third-largest global economy where founders are as likely to build for their own market as for the US.

2. Workforce Disruption & Individualism in the AI Era

• Both hosts grapple with accelerating job displacement due to AI and automation.
  • "If you can't get a job and you can make half the amount of money or double... working for yourself and having a small mom and pop business, you're going to do it. People used to do it, they're going to be doing it again... out of needing to." – Jason Calacanis [00:00, restated at 18:01]
  • "It's creating a low anxiety in the country... where people are like, I kind of feel like my job's going away." – Jason Calacanis [00:00, 18:54]
• Jason previews a multi-part article series on how individuals and society can prepare for mass displacement: learn AI tools or become a founder.

3. Marc Andreessen vs. The Pope: Ethics, AI, and Controversy

• [07:47] The duo dissect Andreessen's online clash after he uses a meme to mock the Pope's ethical warnings about AI.
  • "Marc is saying... I'm going to ask you to explain yourself. And yeah, it just sounds like it just didn't land..." – Jason Calacanis [09:11]
• The debate broadens into how VCs and tech elites handle, or ignore, the moral dimensions of disruptive innovation. Some sharp pushback from Catholic technologists is noted.

4. The (AI) Bubble: Investment Frenzy or Market Correction?

• The mood has shifted—are we in the “party’s over” phase? Jason recounts growing skepticism about massive AI infrastructure investments and the tangled web of company self-dealing (e.g., OpenAI/Nvidia/Oracle).
  • "When we see people start self-dealing... you round tripping the money... how does $300-400 billion show up in Oracle's bank account to pay for this stuff?" – Jason Calacanis [21:01–23:03]
  • "This is peak bubble behavior. We are in a weird bubbly time now." – Jason Calacanis [43:35]
• Macro signals: stock market jitters, inflation, layoffs, but also Q3 growth and robust earnings in the face of uncertainty.

5. Labor, Management, and Tech Culture Clashes

• [33:28] Giga’s $61M Series A raises eyebrows after an ex-employee (Jared Steele) posts serious allegations about culture and business practices (“seven-day workweeks, goat sacrifice, alleged MRR misrepresentations”), prompting lessons in founder humility.
  • "The lying about ARR is securities fraud... These are very serious allegations..." – Jason Calacanis [34:59]
• [39:56] At Conde Nast, unionized writers confront HR—Jason cautions this risky tactic, suggesting both founders and employees are “getting ahead of their skis” in a bubble economy.

6. Startup Success: Standout Growth and IPO-Ready Companies

Ledger (Crypto Hardware/Software)

• Impressive: "Hundreds of millions" in annual revenue, 7 million devices sold, 20% of world’s crypto assets secured.
  • "If it's doing hundreds of millions of dollars, it is at the bottom end of capable of going public." – Jason Calacanis [47:31, 48:54]
• Growing recurring/software side, leveraging cards and wallets, cited as a “unicorn that’s going to listen to everyone.”

1Password (B2B Password Management)

• Now at $400M ARR, up from $250M in 2023, and 75% revenue from business customers.
  • "That's essentially talking about market pull, which is the final stage of product market fit." – Jason Calacanis [31:34]
  • "If these two companies... don't have a billion plus in revenue... would be great to see these go out and have a chance on the market." – Jason Calacanis [50:16]

Mercury (Fintech/Neobank)

• $650M ARR run rate; growing $16.7M/mo, profitable for three years, trusted by sizable customers.
  • "It reminds me in some ways of Robinhood or Uber. Like if you get really good at building apps... you keep delighting the customers..." – Jason Calacanis [53:26]
  • "What if you have another situation like Silicon Valley bank... Probably would be a good idea to keep some in the primary and keep some others in the other." – Jason Calacanis [54:25]

Gamma (AI Presentations)

• $68M raise at $2.1B post, already $100M ARR and 600k paying subs out of 70M users.
  • "Wow, I didn't realize that business was so big." – Jason Calacanis [58:01]
  • "Taking on PowerPoint or Google presentations... With 50 employees... they're making 2 million per employee." – Jason Calacanis [59:27, 60:17]

7. OpenAI: Public or “Uninvestable”?

• Poly Market bets show skepticism over OpenAI IPO by 2026—if valuation stays at $500–750B, Jason sees potential capital-raising problems.
  • "It's got a little bit of valuation... wagers between 500 and 750 billion, which is essentially flat from where they are now... That, to me, implies distress and a need for more capital." – Alex Wilhelm [61:04–61:51]
  • "Is it possible to become so richly valued in the private markets that you're essentially uninvestable unless you go public?" – Alex Wilhelm [63:42]

Notable Quotes & Memorable Moments

• On the new era for workers & founders:

  • "It's every person for themselves. It's going to take a lot of self reliance and rugged individualist." – Jason Calacanis [00:00, 18:01]

• On the AI investment "bubble":

  • "When we see people start self dealing... how does $300-400 billion show up in Oracle's bank account to pay for this stuff?" – Jason Calacanis [21:01]
  • "This is peak bubble behavior. We are in a weird bubbly time now." – Jason Calacanis [43:35]

• On product-market fit:

  • "You don't have true product market fit until it feels like you're wearing a meat suit in a dog park." – Quoted by Alex Wilhelm, via Ayman, former AppSumo CEO [31:01]

• On founder/management conduct:

  • "If you treat them this poorly... these investors could take their money back. This could have like a cataclysmic series of events." – Jason Calacanis [37:07]

• On workplace risks:

  • "If you have one bank, you may have no bank." – Alex Wilhelm [55:26]

Timestamps for Important Segments

| Timestamp | Segment | |--------------|------------------------------------------------------| | [00:00] | The future of work: AI & entrepreneurship | | [02:10] | Jason in Tokyo: Founder University & global insights | | [07:47] | Marc Andreessen vs. the Pope: the meme controversy | | [12:00] | Job loss, automation & how companies handle it | | [18:01] | Explosion of SMBs/self-reliant workers | | [21:01] | AI investing bubble, OpenAI, and roundtripping | | [33:28] | Giga $61M Series A, whistleblower allegations | | [39:56] | Conde Nast labor confrontation | | [43:35] | "Peak bubble" signals in Silicon Valley | | [47:31] | IPO-ready startup: Ledger | | [49:29] | IPO-ready startup: 1Password | | [52:08] | IPO-ready startup: Mercury | | [57:30] | Gamma's rise: AI presentation leader | | [60:37] | AI and startup efficiency: ARR per headcount | | [61:04] | OpenAI IPO: market predictions & risks | | [63:42] | The risk of being "uninvestable" at huge valuations |

Episode Tone & Style

Candid, witty, and at times cautionary, Jason and Alex balance optimism about innovation with hard-nosed skepticism about bubble dynamics and founder hubris. They let their expertise and industry contacts shine, delivering blunt assessments and practical advice for founders on how to survive—and thrive—in uncertain times.

This summary captures the episode’s depth and fast-moving energy, ensuring listeners who missed it are fully equipped with the key context, stories, trends, and actionable lessons.